The Craziest Blind Date Ever

I Brought My Mom & Grandma On My Grouper Blind Date

"I don't have to sleep with anyone, do I?" my 80-year-old Grandma asked.

That was her only question when I asked, at her 80th birthday party, if she would be willing to be my wingwoman on a six-person blind Grouper date. My other wingwoman? My happily married mom. For those of you who aren't familiar with Grouper, this dating app lets you set up a blind date with three strangers in your area. Choose a day and time for the date you want to schedule, and Grouper does the rest: from picking the venue to making the reservation. Grouper even sets your reservation name under something discreet, so that you don't have to tell the hostess what you're really there for.

Grouper asks its daters to bring along two of their best wingwomen. My mom and grandma are the best wingwomen I could ever ask for. Not only are they always on the lookout for potential dates for me (they're still trying to get me to color my hair just so that I can meet the — supposedly straight — handsome hairdresser they both go to), but being around them always puts me at ease. Also, they're an awesome time.

The ability to make the most of any situation is a quality that I find extremely attractive. I think that the way a person handles an unexpected curveball speaks volumes about his or her character, so I decided to do the pitching on this one to see how our dates would react.Related: 10 Worst Tinder Dates Ever (As Witnessed By Bartenders)

I also wanted to give my mom and grandma a taste of what dating looks like in 2015. The fact that in just a few clicks, I can have a date set with three strangers on any given night in NYC is pretty wild.

A big shout out to my girl Challen, Grouper's founder, who worked with me to schedule and reschedule this date during the launch of the brand's new app, while the team was still working out the kinks. (I doubt Tinder would have returned my texts if I had a date suddenly cancel.)

Illustrated by Jasmin Valcourt.

Our Big NightAt 9 p.m. on a Thursday on the Lower East Side, my mom, grandma, and I arrived at the swanky lounge that Grouper chose for us, told the hostess the name we were given, ordered a round of cocktails, and took a seat. Shortly after, a group of three guys showed up looking confused. They were seated at the table next to us.

Advertisement

For a minute, I thought maybe these were the guys we'd been matched with, and that they had decided not to go through with it. When I asked our waitress, though, she assured me she was going to bring our group over when they got here, and that she wouldn't let them chicken out. My kind of girl, I thought. Finally, three guys showed up and were seated with us. I wish I had taken a reaction shot, because the looks on their faces were really priceless. My mom and grandma introduced themselves as Pam and Laura, and the men made their introductions as well (Brian, Tony, and Mike).

Tony made a beeline for the bathroom, where I assumed he was texting his crew to evaluate what to make of their current situation. But, Brian and Mike ordered cocktails, and we started making small talk. "So, how do you all know each other?" Mike asked us. "We go way back," I told him.

Laura and Pam laughed. "No, but seriously, you're not going to tell us?" Mike said."If you had to guess, what would you say?" I asked him, thinking our resemblance was pretty obvious."You're sisters?" Brian asked, followed by, "Where's your mom tonight? Does she know you're here?" That got a good laugh from us as well. When Tony returned, he asked what he had missed, and Brian filled him on how we were related."Wait," Tony said, dead serious, "You're sisters?"

"Tony is our smartest friend," Brian told us, which made us all laugh again. We had definitely lucked out with this group.

Illustrated by Jasmin Valcourt.

Our ConversationMy mom once told me the story of the first date she ever went on. Apparently, she had barely said a word the entire time, and her date broke things off the next day, telling my mom that she was too quiet. That woman is not the same Pam who came out with me on this Grouper date. My mom was the star of this Grouper, telling the guys all about her time running the Italian restaurant that my family used to own on the Upper East Side, and her dream of owning a food truck.

My grandma is one of those people who has a way of making you feel good about yourself, no matter what. When you talk to her, you feel like you're really being heard, and that what you have to say is interesting, even when you're not so sure that it is. She worked that magic on our dates, asking each of the guys what they do, where they live, and what they studied during college, as well as a very important question: "Who here is Italian?" (only Tony, and only one eighth — but my grandma didn't hold that against him). As we listened to the guys tell funny stories from their college days, I felt like I had a front-row seat to a sketch comedy show — not like I was here on a blind Grouper date. As we started to like these guys more and more, my mom felt increasingly guilty that we were still lying to them about what was really going on here. So, she made me spill the beans.

"My wife and kids can't know about this. Where are you publishing this?" — Brian (he was kidding)

Since our secret was now out in the open, I was dying to find out what they thought when they first saw us."Honestly," Tony said, "When we first got here, I went straight to the bathroom and texted everyone, saying, 'I'm really into Pam.'"

Pam, my mom, insists that he was kidding, but I'm not so sure. Brian told us that the three of them actually did have an exit strategy for if they wanted to bail: a nonchalant sign they were going to use to signal each other, just in case. When we asked him to show it to us, he made what looked like big S.O.S. circles with his arms in the air, which cracked us up. We eventually called it a night and said our goodbyes. My mom handed out cards for our family's restaurant on Long Island, and insisted that if the guys are ever in the area, they should come in and let her buy them some dinner. I got contact info from all three of the guys — in order to send them this article, of course.The Verdict"So, which one are you going to text?" my grandma asked once they had left. Honestly, I kind of assumed that after I pulled a stunt like this, none of these guys would be interested in a second date. I mean, what if I brought my dad along next time or something? (Actually, after he reads this, my dad might want to have a few words with Tony.)

But, in all seriousness, I hope this isn't the last I've seen of Mike, Tony, and Brian, who are responsible for one of the best dates I've ever been on, hands down. And, you know what? I think they might just be thinking the same about Laura, Pam, and me. I hit the mom-and-grandma jackpot — and that fact is never lost on me.